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Anal Penetration: The Basics

Getting started with anal penetration can sometimes feel a little scary, but it takes just a few simple steps to make it easy and pleasurable. These tips work well for solo play and exploring with a partner.

Getting Ready

Fingers are a great way to get started since you have much more control over them than a toy. Be sure to trim your nails and check for rough edges by running them across your lips. If you feel anything rough, file it down. It’s also a good idea to put on a glove, not just for cleanliness, but also to smooth everything out.

Start off with some external massage. Rub the perineum and inner thighs with your fingers or your thumbs. Different men like different strokes, so try a few and ask him which he prefers. You can also include some penis stimulation, either with your other hand or your mouth. A little familiar pleasure can help him relax into the experience and enjoy anal penetration even more.

Try massaging the external anal muscle before doing any insertion. Circles or gentle tapping often work well. Be sure to use a lubricant to start getting things slippery. Have him take a deep breath and bear down on the exhale- you’ll feel his anus pucker out a little bit. When he inhales, you’ll feel it pull back in. That’s useful when you get ready for insertion. Tease his anus a bit, instead of just going for it. Drawing things out will increase his arousal and intensify the sensations.

Breathe Into It

When you’re both ready for penetration, get some more lubricant on your finger. Place your finger perpendicular to his anus, with your fingertip resting on the opening. Have him take another breath and bear down on the exhale (the same motion as going to the bathroom). As his anus puckers out, bend your fingertip so that is slides just inside. Think of it as him putting his anus on your finger, instead of pushing the finger into the anus. Once he finishes exhaling, hold still for a moment. Have him do it again as you slide a little further in, and repeat as needed.

You’ll be able to feel both rings of the anal muscles, which are about an inch or so apart (2.5 cm). Before you slide further in, make a small circle and massage all around the anus. Try clockwise and counterclockwise. Or massage up and down, and then left and right. You might notice a spot that feels tight or tender or warm. You can help the muscles relax by holding firm pressure against the tight spots for 45-60 seconds. You’ll probably feel the muscles release more quickly when you do than than when you vigorously rub them. Remind him to keep breathing and time your movements with his breath.

As his anus relaxes, try sliding your finger gently in and out. Or vibrate it gently. Or return to external massage for a few minutes before going back in. Or insert your finger partway and curl the tip. If you have difficulty keeping your rhythm, have him stroke his penis so you can focus on what you’re doing. Or put on some sexy music with a steady beat that you can follow.

Once You’re In

When his anus begins to relax, slide your finger all the way in and massage his prostate. There are lots of different prostate massage techniques that work well with just one finger. Of course, you can also add another finger when he’s ready. Check with him first- anal penetration works best when the receiver has control over the speed that things are moving at. Have him take a deep breath and gently slide your finer out on the exhale. Get some more lubricant on your fingers and do the same thing you did on the initial insertion- time it with his exhalation and bearing down. It’ll probably be easier, especially if he’s had some experience with it, but don’t rush.

Some men enjoy anal stimulation in and of itself, so try it and see how he likes it. The anus has lots of sensitive nerve endings, so it’s worth exploring. And of course, once he’s relaxed enough to let your fingers in, prostate pleasure is just a small step away.

If you’re looking for some more tips for easy anal penetration or for prostate stimulation, we have plenty to offer in The Ultimate Guide to Prostate Pleasure so pick up your copy today and get ready for a fun time!